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Establishing the True Structure of the Sorbicillinoid-Derived Isolate Rezishanone C by Total Synthesis

Journal Article


Abstract


  • The enantiomer, ent-4, of the true structure, 4, of the sorbicillinoid rezishanone C (sorbivinetone) has been synthesized from a homochiral cis-1,2-dihydrocatechol that is itself generated through the whole-cell biotransformation of toluene. These studies together with dispersion-corrected DFT calculations support the proposal that rezishanone C is an artefact of the isolation process and arises through a Diels���Alder reaction between ethyl vinyl ether and sorbicillinol (3).

Publication Date


  • 2017

Citation


  • Yan, Q., Banwell, M. G., Coote, M. L., Lee, R., & Willis, A. C. (2017). Establishing the True Structure of the Sorbicillinoid-Derived Isolate Rezishanone C by Total Synthesis. Chemistry - An Asian Journal, 12(13), 1480-1484. doi:10.1002/asia.201700456

Scopus Eid


  • 2-s2.0-85020183731

Start Page


  • 1480

End Page


  • 1484

Volume


  • 12

Issue


  • 13

Place Of Publication


Abstract


  • The enantiomer, ent-4, of the true structure, 4, of the sorbicillinoid rezishanone C (sorbivinetone) has been synthesized from a homochiral cis-1,2-dihydrocatechol that is itself generated through the whole-cell biotransformation of toluene. These studies together with dispersion-corrected DFT calculations support the proposal that rezishanone C is an artefact of the isolation process and arises through a Diels���Alder reaction between ethyl vinyl ether and sorbicillinol (3).

Publication Date


  • 2017

Citation


  • Yan, Q., Banwell, M. G., Coote, M. L., Lee, R., & Willis, A. C. (2017). Establishing the True Structure of the Sorbicillinoid-Derived Isolate Rezishanone C by Total Synthesis. Chemistry - An Asian Journal, 12(13), 1480-1484. doi:10.1002/asia.201700456

Scopus Eid


  • 2-s2.0-85020183731

Start Page


  • 1480

End Page


  • 1484

Volume


  • 12

Issue


  • 13

Place Of Publication